CA1065879A - PREPARATION DE .beta.-ACYLPYRROLES - Google Patents

PREPARATION DE .beta.-ACYLPYRROLES

Info

Publication number: CA1065879A
Authority: CA; Canada
Prior art keywords: acid; group; loweralkyl; member selected; anhydrous
Prior art date: 1975-06-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA254,455A

Other languages

English (en)

Inventor

John R. Carson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Janssen Pharmaceuticals Inc

Original Assignee

McNeilab Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-06-27

Filing date

1976-06-09

Publication date

1979-11-06

1976-06-09 Application filed by McNeilab Inc filed Critical McNeilab Inc

1979-11-06 Application granted granted Critical

1979-11-06 Publication of CA1065879A publication Critical patent/CA1065879A/fr

Status Expired legal-status Critical Current

Links

KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims abstract description 46
238000002360 preparation method Methods 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 27
239000002253 acid Substances 0.000 claims abstract description 22
230000001590 oxidative effect Effects 0.000 claims abstract description 14
238000010438 heat treatment Methods 0.000 claims abstract description 5
-1 trifluoromethylphenyl Chemical group 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 7
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 6
125000006501 nitrophenyl group Chemical group 0.000 claims description 6
229920000137 polyphosphoric acid Polymers 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
229940098779 methanesulfonic acid Drugs 0.000 claims description 5
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 8
125000001475 halogen functional group Chemical group 0.000 claims 7
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
230000001131 transforming effect Effects 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
150000001875 compounds Chemical class 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000047 product Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000003233 pyrroles Chemical class 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
238000010992 reflux Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000012267 brine Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000835 fiber Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000010410 layer Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
230000008707 rearrangement Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
FAVMHHURTMOBPA-UHFFFAOYSA-N (4-chlorophenyl)-(1,3,5-trimethylpyrrol-2-yl)methanone Chemical compound C1=C(C)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C FAVMHHURTMOBPA-UHFFFAOYSA-N 0.000 description 2
YTVORWPYOKKVAM-UHFFFAOYSA-N (4-chlorophenyl)-(1h-pyrrol-2-yl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CN1 YTVORWPYOKKVAM-UHFFFAOYSA-N 0.000 description 2
CHNYVNOFAWYUEG-UHFFFAOYSA-N 1h-pyrrole-3-carbaldehyde Chemical compound O=CC=1C=CNC=1 CHNYVNOFAWYUEG-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229930194542 Keto Natural products 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
239000006096 absorbing agent Substances 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000011368 organic material Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
YLDDGZQCRPTKIH-UHFFFAOYSA-N (1-methylpyrrol-2-yl)-phenylmethanone Chemical compound CN1C=CC=C1C(=O)C1=CC=CC=C1 YLDDGZQCRPTKIH-UHFFFAOYSA-N 0.000 description 1
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
SZYIVZGXCXFXDN-UHFFFAOYSA-N 1-(1-methylpyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C=CN(C)C=1 SZYIVZGXCXFXDN-UHFFFAOYSA-N 0.000 description 1
VPUAYOJTHRDUTK-UHFFFAOYSA-N 1-ethylpyrrole Chemical compound CCN1C=CC=C1 VPUAYOJTHRDUTK-UHFFFAOYSA-N 0.000 description 1
BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
TVCXVUHHCUYLGX-UHFFFAOYSA-N 2-Methylpyrrole Chemical compound CC1=CC=CN1 TVCXVUHHCUYLGX-UHFFFAOYSA-N 0.000 description 1
NZWUDXWOUPEZMR-UHFFFAOYSA-N 3-(2-nitroethenyl)-1h-pyrrole Chemical compound [O-][N+](=O)C=CC=1C=CNC=1 NZWUDXWOUPEZMR-UHFFFAOYSA-N 0.000 description 1
FARSXMMESQDZMY-UHFFFAOYSA-N 4-chloro-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(Cl)C=C1 FARSXMMESQDZMY-UHFFFAOYSA-N 0.000 description 1
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
241000610375 Sparisoma viride Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
206010042496 Sunburn Diseases 0.000 description 1
BHKIAROAKGHQMX-UHFFFAOYSA-N [C].CCCCCC Chemical compound [C].CCCCCC BHKIAROAKGHQMX-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
229940125716 antipyretic agent Drugs 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006473 carboxylation reaction Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
UUYYJWFAHPQMJY-UHFFFAOYSA-N cyanomethoxy-oxido-oxophosphanium Chemical compound [O-][P+](=O)OCC#N UUYYJWFAHPQMJY-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
QQILXENAYPUNEA-UHFFFAOYSA-M tolmetin sodium dihydrate Chemical compound O.O.[Na+].C1=CC(C)=CC=C1C(=O)C1=CC=C(CC([O-])=O)N1C QQILXENAYPUNEA-UHFFFAOYSA-M 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyrrole Compounds (AREA)

CA254,455A 1975-06-27 1976-06-09 PREPARATION DE .beta.-ACYLPYRROLES Expired CA1065879A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/590,996 US4002643A (en)	1975-06-27	1975-06-27	Preparation of β-acyl pyrroles

Publications (1)

Publication Number	Publication Date
CA1065879A true CA1065879A (fr)	1979-11-06

Family

ID=24364603

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA254,455A Expired CA1065879A (fr)	1975-06-27	1976-06-09	PREPARATION DE .beta.-ACYLPYRROLES

Country Status (8)

Country	Link
US (1)	US4002643A (fr)
JP (1)	JPS525762A (fr)
CA (1)	CA1065879A (fr)
DE (1)	DE2628476A1 (fr)
DK (1)	DK283476A (fr)
FR (1)	FR2315501A1 (fr)
GB (1)	GB1541493A (fr)
SE (1)	SE7607239L (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4299770A (en) *	1980-05-29	1981-11-10	Mallinckrodt, Inc.	Recovery of substituted pyrrole acetate
US5043348A (en) *	1987-04-24	1991-08-27	Cassella Aktiengesellschaft	Pyrrolealdehydes, their preparation and their use
DE4211531A1 (de) *	1992-04-06	1993-10-07	Cassella Ag	Verfahren zur Herstellung von Pyrrolderivaten
US5681795A (en) *	1994-03-02	1997-10-28	Zeneca Limited	3-benzoyl pyrrole and pyrazole herbicides
US5512537A (en) *	1994-03-02	1996-04-30	Zeneca Limited	2-benzoyl pyrrole and benzoyl imidazole herbicides
JP3663382B2 (ja) *	2000-02-15	2005-06-22	スージェン・インコーポレーテッド	ピロール置換２−インドリノン蛋白質キナーゼ阻害剤
AR042586A1 (es) *	2001-02-15	2005-06-29	Sugen Inc	3-(4-amidopirrol-2-ilmetiliden)-2-indolinona como inhibidores de la protein quinasa; sus composiciones farmaceuticas; un metodo para la modulacion de la actividad catalitica de la proteinquinasa; un metodo para tratar o prevenir una afeccion relacionada con la proteinquinasa
BR0213185A (pt)	2001-10-10	2004-09-14	Sugen Inc	Derivados de 3-[4-(heterociclila substituìda)-pirrol-2-ilmetilideno]2-indolinona como inibidores de cinase

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3644631A (en) *	1969-05-13	1972-02-22	Endo Lab	Therapeutic methods utilizing aryl pyrrol-3-yl ketones

1975
- 1975-06-27 US US05/590,996 patent/US4002643A/en not_active Expired - Lifetime
1976
- 1976-05-14 GB GB20074/76A patent/GB1541493A/en not_active Expired
- 1976-06-04 FR FR7617084A patent/FR2315501A1/fr active Granted
- 1976-06-09 CA CA254,455A patent/CA1065879A/fr not_active Expired
- 1976-06-23 SE SE7607239A patent/SE7607239L/xx unknown
- 1976-06-24 DK DK283476A patent/DK283476A/da not_active Application Discontinuation
- 1976-06-25 JP JP51074572A patent/JPS525762A/ja active Pending
- 1976-06-25 DE DE19762628476 patent/DE2628476A1/de active Pending

Also Published As

Publication number	Publication date
DK283476A (da)	1976-12-28
DE2628476A1 (de)	1977-01-13
FR2315501B1 (fr)	1979-07-20
SE7607239L (sv)	1976-12-28
FR2315501A1 (fr)	1977-01-21
US4002643A (en)	1977-01-11
GB1541493A (en)	1979-03-07
JPS525762A (en)	1977-01-17

Publication	Publication Date	Title
US4325962A (en)	1982-04-20	Pharmaceutical compositions comprising a pyrazole derivative and method of use
EP1178969B1 (fr)	2005-07-13	Ligands de recepteur de la gastrine et de la cholecystokinine
CA1094084A (fr)	1981-01-20	Composes a base d'acide 1-alkyle a chaine courte-5- aroylpyrrole-2-acetique halosubstitues
US3810906A (en)	1974-05-14	N1-heteroacylated phenylhydrazines
IE48935B1 (en)	1985-06-26	Antiinflammatory 4,5-diaryl-2-nitroimidazoles,method for their preparation and pharmaceutical composition containing them
CA1065879A (fr)	1979-11-06	PREPARATION DE .beta.-ACYLPYRROLES
JPS5951269A (ja)	1984-03-24	トリフエニルイミダゾリルオキシアルカン酸およびその誘導体
CA1267893A (fr)	1990-04-17	Derives de substitution en 11 de 5h,11h-pyrrolo ¬2,1-c\|¬1,4\|benzoxazepines; methode de preparation et utilisation comme medicaments
EP0000649B1 (fr)	1981-03-25	1,2-Dihydro-3H-pyrrolo(1,2-a)pyrrole-1-carbonitriles substitués en position 5 et procédé pour leur conversion en 1-acides carboxyliques correspondants
DE1620442C3 (de)	1975-07-03	Verfahren zur Herstellung von 1-Acylindolverbindungen
DE2708111A1 (de)	1977-09-01	Aminoalkylpyrrolbenzoxaazaalkane
DE2407671C2 (de)	1983-12-01	Kondensierte N-Phenylpyrrole, Verfahren zu ihrer Herstellung und deren Verwendung
CA1235703A (fr)	1988-04-26	Derives de substitution en 6 de 6h-dibenzo/b.d/pyranne; methode de preparation
DD295373A5 (de)	1991-10-31	Verfahren zur herstellung von alpha-cyan-beta-oxopropionamiden
JP2858940B2 (ja)	1999-02-17	新規ベンゾトリアゾール化合物の製造方法
KR850000845B1 (ko)	1985-06-17	피롤리딘 유도체의 제조방법
US4361579A (en)	1982-11-30	Organogermanium compounds
DD243277A5 (de)	1987-02-25	Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate
Suzuki et al.	1986	Syntheses of 2-Aryl-4-(3-thienyl) imidazole Derivatives with Antiinflammatory Preperties
CA1209989A (fr)	1986-08-19	Composes non steroidiens utilises comme anti-inflammatoires et analgesiques
JPS6479157A (en)	1989-03-24	Novel 2-pyrazolines and remedy for cerebrovascular disorder containing said compound as active component
CA1146566A (fr)	1983-05-17	Procede d'obtention de pyrroles substitues
EP0661263B1 (fr)	2001-04-25	Procédé pour la préparation de 2,4,5 tribromopyrrole-3-carbonitrile
CA1191135A (fr)	1985-07-30	Derives 2-pyrrolin-3-carbonitril-, procede de preparation et composes pharmaceutiques les contenant
US4255335A (en)	1981-03-10	Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid derivatives